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J-GLOBAL ID：201902226828133456   Reference number：19A0851094

DESIGN AND SYNTHESIS OF A DNA-LIKE STRUCTURE COMPOSED OF ALKYNYL C-NUCLEOTIDE WITH 2-AMINOPYRIMIDIN-4-ONE AS A NUCLEOBASE

核酸塩基として2-アミノピリミジン-4-オンを有するアルキニルC-ヌクレオチドからなるDNA様構造の設計と合成

Author (3)： KUROSAKI Fumihiro (Univ. Toyama, Toyama, JPN) ,  CHIBA Junya (Univ. Toyama, Toyama, JPN) ,  INOUYE Masahiko (Univ. Toyama, Toyama, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 97  Issue： 2  Page： 1149-1156  Publication year： Sep. 01, 2018 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： solid phase synthesis ,  DNA synthesis ,  *C-nucleoside ,  *acetylenic compound ,  deoxyribonucleoside ,  pyrimidine nucleoside ,  pyrimidine base ,  oligomer ,  nucleic acid base ,  DNA

JST classification (2)： Pyrimidines  (CF07103W) ,  Nucleosides,nucleotides  (CF10060K)

Substance index (4)： 2-amino-6-{2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]ethynyl}-3H-pyrimidin-4-one ,  6-[[5-O-[Bis(4-methoxyphenyl)(phenyl)methyl]-2-deoxy-β-D-ribofuranosyl]ethynyl]-2-[(dimethylamino)methyleneamino]pyrimidine-4(3H)-one ,  N'-(4-{2-[(2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-{[(2-cyanoethoxy)(diisopropylamino)phosphanyl]oxy}oxolan-2-yl]ethynyl}-6-oxo-1H-pyrimidin-2-yl)-N,N-dimethylmethanimidamide ,  N'-(4-iodo-6-oxo-1H-pyrimidin-2-yl)-N,N-dimethylmethanimidamide

Reference (7)：

• S. A. Benner, Acc. Chem. Res., 2004, 37, 784; J. Chiba and M. Inouye, 'Exotic DNAs Made of Nonnatural Bases and Natural Phosphodiester Bonds' in Chemistry and Biology of Artificial Nucleic Acids, Vol. 61, ed. by M. Egli and P. Herdewijn, Wiley-VCH, Weinheim, 2012, pp. 135-158; M. Winnacker and E. T. Kool, Angew. Chem. Int. Ed., 2013, 52, 12498.
• H. Abe, M. Takase, Y. Doi, S. Matsumoto, M. Furusyo, and M. Inouye, Eur. J. Org. Chem., 2005, 2931; K. Fujimoto, T. Toyoshi, Y. Doi, and M. Inouye, Mat. Sci. Eng. C, 2007, 27, 142; M. Inouye, Y. Doi, J. Azuchi, W. Shirato, J. Chiba, and H. Abe, Heterocycles, 2011, 82, 1137.
• Y. Doi, J. Chiba, T. Morikawa, and M. Inouye, J. Am. Chem. Soc., 2008, 130, 8762; J. Chiba and M. Inouye, Chem. Biodivers., 2010, 7, 259; J. Chiba, W. Shirato, Y. Yamade, B.-S. Kim, S. Matsumoto, and M. Inouye, Tetrahedron, 2012, 68, 9045; W. Shirato, J. Chiba, and M. Inouye, Chem. Commun., 2015, 51, 7043; J. Chiba and M. Inouye, 'Synthesis of nonnatural oligonucleotides exclusively of alkynyl C-nucleosides with nonnatural bases' in Curr. Protoc. Nucleic Acid Chem., Vol. 61, ed. by M. Egli, P. Herdewijn, A. Matsuda, and Y. S. Sanghvi, Wiley Online Library, Weinheim, 2015, pp. 4.62.1-4.62.22.
• J. Chiba, S. Takeshima, K. Mishima, H. Maeda, Y. Nanai, K. Mizuno, and M. Inouye, Chem. Eur. J., 2007, 13, 8124.
• For other synthetic examples of alkynyl C-nucleosides by Sonogashira reaction, see: M. F. A. Adamo and R. Pergoli, Org. Lett., 2007, 9, 4443; D. Heinrich, T. Wagner, and U. Diederichsen, Org. Lett., 2007, 9, 5311; T. Bobula, M. Hocek, and M. Kotora, Tetrahedron, 2010, 66, 530; K. Fujimoto, S. Aizawa, I. Oota, J. Chiba, and M. Inouye, Chem. Eur. J., 2010, 16, 2401; J. Chiba, A. Sakai, S. Yamada, K. Fujimoto, and M. Inouye, Chem. Commun., 2013, 49, 6454.

Terms in the title (4)： 核酸塩基 ,  ヌクレオチド ,  DNA ,  設計